#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025527.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025527
loop_
_publ_author_name
'Lang Liu'
'Xiangyun Xie'
'Dianzeng Jia'
'Jixi Guo'
'Xiaolin Xie'
_publ_section_title
;
 Synthesis and Properties of a Novel Photochromic Compound with Modulated
 Fluorescence in the Solid State
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4742
_journal_page_last               4747
_journal_paper_doi               10.1021/jo100372z
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C29 H22 Br N5 O2'
_chemical_formula_weight         552.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.370(3)
_cell_angle_beta                 93.653(3)
_cell_angle_gamma                103.860(3)
_cell_formula_units_Z            4
_cell_length_a                   10.8724(12)
_cell_length_b                   16.0650(19)
_cell_length_c                   16.651(2)
_cell_measurement_temperature    153(2)
_cell_volume                     2528.3(5)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_sigmaI/netI    0.1421
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20351
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  0.6353
_exptl_absorpt_correction_T_min  0.4902
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       0.0081(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         9105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1107P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.2335
_reflns_number_gt                4593
_reflns_number_total             9105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100372z_si_002.cif
_cod_data_source_block           g0424
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2528.2(5)
_cod_database_code               4025527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.55847(7) 0.41320(6) 0.27308(5) 0.0607(3) Uani 1 1 d . . .
O1 O 0.6489(5) 0.9732(4) 0.3707(3) 0.0560(13) Uani 1 1 d . . .
H1O H 0.6074 0.9359 0.3896 0.067 Uiso 1 1 calc R . .
O2 O 0.9500(4) 0.9802(3) 0.5804(3) 0.0463(11) Uani 1 1 d . . .
N1 N 0.7242(5) 0.9627(4) 0.2406(4) 0.0468(14) Uani 1 1 d . . .
N2 N 0.7690(5) 0.9032(4) 0.1703(4) 0.0455(14) Uani 1 1 d . . .
N3 N 0.7464(5) 0.7907(4) 0.3898(3) 0.0453(14) Uani 1 1 d . . .
N4 N 0.8258(5) 0.8803(4) 0.4441(3) 0.0439(13) Uani 1 1 d . . .
H4N H 0.8439 0.9244 0.4247 0.053 Uiso 1 1 calc R . .
N5 N 0.8414(5) 0.8269(4) 0.5515(3) 0.0449(14) Uani 1 1 d . . .
H5N H 0.7953 0.7720 0.5075 0.054 Uiso 1 1 calc R . .
C1 C 0.7404(7) 1.1309(6) 0.3260(6) 0.062(2) Uani 1 1 d . . .
H1 H 0.7555 1.1264 0.3807 0.075 Uiso 1 1 calc R . .
C2 C 0.7413(9) 1.2181(7) 0.3262(7) 0.083(3) Uani 1 1 d . . .
H2 H 0.7581 1.2739 0.3815 0.099 Uiso 1 1 calc R . .
C3 C 0.7176(8) 1.2232(8) 0.2459(7) 0.083(3) Uani 1 1 d . . .
H3 H 0.7186 1.2828 0.2466 0.099 Uiso 1 1 calc R . .
C4 C 0.6926(7) 1.1431(7) 0.1653(7) 0.070(2) Uani 1 1 d . . .
H4 H 0.6773 1.1474 0.1105 0.084 Uiso 1 1 calc R . .
C5 C 0.6899(7) 1.0563(6) 0.1647(5) 0.058(2) Uani 1 1 d . . .
H5 H 0.6694 1.0001 0.1094 0.070 Uiso 1 1 calc R . .
C6 C 0.7172(6) 1.0515(5) 0.2449(5) 0.0483(17) Uani 1 1 d . . .
C7 C 0.6970(6) 0.9234(5) 0.2990(4) 0.0456(17) Uani 1 1 d . . .
C8 C 0.7240(6) 0.8381(5) 0.2679(4) 0.0402(15) Uani 1 1 d . . .
C9 C 0.7656(6) 0.8265(5) 0.1846(4) 0.0426(16) Uani 1 1 d . . .
C10 C 0.8065(6) 0.7481(5) 0.1195(4) 0.0420(16) Uani 1 1 d . . .
C11 C 0.7942(6) 0.7348(5) 0.0305(4) 0.0489(18) Uani 1 1 d . . .
H11 H 0.7571 0.7742 0.0133 0.059 Uiso 1 1 calc R . .
C12 C 0.8362(6) 0.6639(5) -0.0326(5) 0.0533(19) Uani 1 1 d . . .
H12 H 0.8285 0.6552 -0.0929 0.064 Uiso 1 1 calc R . .
C13 C 0.8891(7) 0.6059(5) -0.0078(5) 0.0548(18) Uani 1 1 d . . .
H13 H 0.9177 0.5573 -0.0507 0.066 Uiso 1 1 calc R . .
C14 C 0.9000(7) 0.6195(6) 0.0804(5) 0.0571(19) Uani 1 1 d . . .
H14 H 0.9350 0.5792 0.0974 0.069 Uiso 1 1 calc R . .
C15 C 0.8607(6) 0.6909(5) 0.1440(5) 0.0483(17) Uani 1 1 d . . .
H15 H 0.8711 0.7005 0.2045 0.058 Uiso 1 1 calc R . .
C16 C 0.7024(6) 0.7693(5) 0.3069(4) 0.0440(16) Uani 1 1 d . . .
C17 C 0.6225(6) 0.6686(5) 0.2526(4) 0.0449(16) Uani 1 1 d . . .
C18 C 0.6291(6) 0.5978(5) 0.2793(4) 0.0452(17) Uani 1 1 d . . .
H18 H 0.6893 0.6139 0.3310 0.054 Uiso 1 1 calc R . .
C19 C 0.5520(6) 0.5072(5) 0.2334(4) 0.0431(16) Uani 1 1 d . . .
C20 C 0.4700(7) 0.4809(6) 0.1530(5) 0.059(2) Uani 1 1 d . . .
H20 H 0.4186 0.4166 0.1187 0.070 Uiso 1 1 calc R . .
C21 C 0.4646(6) 0.5491(6) 0.1244(5) 0.0538(18) Uani 1 1 d . . .
H21 H 0.4091 0.5319 0.0701 0.065 Uiso 1 1 calc R . .
C22 C 0.5394(6) 0.6421(5) 0.1742(4) 0.0495(18) Uani 1 1 d . . .
H22 H 0.5338 0.6889 0.1543 0.059 Uiso 1 1 calc R . .
C23 C 0.8765(6) 0.8996(5) 0.5296(4) 0.0425(16) Uani 1 1 d . . .
C24 C 0.8682(6) 0.8262(5) 0.6354(4) 0.0466(17) Uani 1 1 d . . .
C25 C 0.9580(6) 0.9003(6) 0.7076(4) 0.0497(18) Uani 1 1 d . . .
H25 H 1.0052 0.9556 0.7030 0.060 Uiso 1 1 calc R . .
C26 C 0.9770(7) 0.8913(6) 0.7866(5) 0.057(2) Uani 1 1 d . . .
H26 H 1.0388 0.9412 0.8364 0.068 Uiso 1 1 calc R . .
C27 C 0.9093(8) 0.8131(6) 0.7944(5) 0.063(2) Uani 1 1 d . . .
H27 H 0.9241 0.8093 0.8495 0.076 Uiso 1 1 calc R . .
C28 C 0.8198(9) 0.7394(6) 0.7239(5) 0.073(2) Uani 1 1 d . . .
H28 H 0.7741 0.6843 0.7296 0.088 Uiso 1 1 calc R . .
C29 C 0.7966(7) 0.7461(6) 0.6437(5) 0.060(2) Uani 1 1 d . . .
H29 H 0.7327 0.6966 0.5950 0.072 Uiso 1 1 calc R . .
Br1A Br 0.36552(7) 1.14316(6) 0.09244(5) 0.0682(3) Uani 1 1 d . . .
O1A O 0.1128(5) 0.8710(4) 0.4098(3) 0.0539(12) Uani 1 1 d . . .
H1AO H 0.1031 0.9205 0.4079 0.065 Uiso 1 1 calc R . .
O2A O 0.5015(4) 1.1136(3) 0.5578(3) 0.0450(11) Uani 1 1 d . . .
N1A N 0.1286(5) 0.7252(4) 0.3071(4) 0.0455(14) Uani 1 1 d . . .
N2A N 0.1773(5) 0.6848(4) 0.2295(3) 0.0448(13) Uani 1 1 d . . .
N3A N 0.3243(5) 1.0207(4) 0.3417(3) 0.0413(13) Uani 1 1 d . . .
N4A N 0.3708(5) 1.0221(4) 0.4220(3) 0.0434(13) Uani 1 1 d . . .
H4AN H 0.3495 0.9715 0.4323 0.052 Uiso 1 1 calc R . .
N5AN N 0.4707(5) 1.1813(4) 0.4628(3) 0.0456(14) Uani 1 1 d . . .
H5A H 0.4303 1.1676 0.4094 0.055 Uiso 1 1 calc R . .
C1A C 0.0538(7) 0.6988(6) 0.4323(5) 0.059(2) Uani 1 1 d . . .
H1A H 0.0941 0.7641 0.4727 0.070 Uiso 1 1 calc R . .
C2A C -0.0121(8) 0.6331(7) 0.4621(6) 0.071(2) Uani 1 1 d . . .
H2A H -0.0147 0.6543 0.5241 0.085 Uiso 1 1 calc R . .
C3A C -0.0715(7) 0.5409(7) 0.4045(7) 0.076(3) Uani 1 1 d . . .
H3A H -0.1176 0.4986 0.4260 0.091 Uiso 1 1 calc R . .
C4A C -0.0653(8) 0.5078(7) 0.3140(6) 0.077(3) Uani 1 1 d . . .
H4A H -0.1047 0.4423 0.2739 0.093 Uiso 1 1 calc R . .
C5A C -0.0018(7) 0.5702(6) 0.2821(5) 0.059(2) Uani 1 1 d . . .
H5A H 0.0010 0.5487 0.2201 0.071 Uiso 1 1 calc R . .
C6A C 0.0571(6) 0.6639(5) 0.3420(5) 0.0488(17) Uani 1 1 d . . .
C7A C 0.1528(6) 0.8207(5) 0.3363(4) 0.0478(17) Uani 1 1 d . . .
C8A C 0.2194(6) 0.8452(5) 0.2764(4) 0.0439(16) Uani 1 1 d . . .
C9A C 0.2297(6) 0.7576(5) 0.2119(4) 0.0416(15) Uani 1 1 d . . .
C10A C 0.2929(6) 0.7409(5) 0.1321(4) 0.0415(16) Uani 1 1 d . . .
C11A C 0.2430(6) 0.6568(5) 0.0543(4) 0.0492(17) Uani 1 1 d . . .
H11A H 0.1699 0.6092 0.0524 0.059 Uiso 1 1 calc R . .
C12A C 0.3000(7) 0.6419(6) -0.0211(5) 0.064(2) Uani 1 1 d . . .
H12A H 0.2679 0.5833 -0.0739 0.076 Uiso 1 1 calc R . .
C13A C 0.4026(7) 0.7124(5) -0.0187(5) 0.057(2) Uani 1 1 d . . .
H13A H 0.4393 0.7033 -0.0709 0.069 Uiso 1 1 calc R . .
C14A C 0.4527(6) 0.7958(5) 0.0581(5) 0.0518(18) Uani 1 1 d . . .
H14A H 0.5250 0.8437 0.0594 0.062 Uiso 1 1 calc R . .
C15A C 0.3980(6) 0.8105(5) 0.1340(4) 0.0456(16) Uani 1 1 d . . .
H15A H 0.4327 0.8684 0.1873 0.055 Uiso 1 1 calc R . .
C16A C 0.2591(5) 0.9395(5) 0.2759(4) 0.0407(15) Uani 1 1 d . . .
C17A C 0.2239(6) 0.9495(5) 0.1913(4) 0.0412(15) Uani 1 1 d . . .
C18A C 0.3003(6) 1.0243(5) 0.1784(4) 0.0425(16) Uani 1 1 d . . .
H18A H 0.3759 1.0667 0.2211 0.051 Uiso 1 1 calc R . .
C19A C 0.2665(6) 1.0372(6) 0.1037(4) 0.0504(18) Uani 1 1 d . . .
C20A C 0.1606(7) 0.9740(6) 0.0388(5) 0.060(2) Uani 1 1 d . . .
H20A H 0.1374 0.9829 -0.0124 0.071 Uiso 1 1 calc R . .
C21A C 0.0879(6) 0.8964(6) 0.0501(5) 0.058(2) Uani 1 1 d . . .
H21A H 0.0161 0.8511 0.0052 0.070 Uiso 1 1 calc R . .
C22A C 0.1195(6) 0.8845(6) 0.1263(4) 0.0508(18) Uani 1 1 d . . .
H22A H 0.0691 0.8317 0.1335 0.061 Uiso 1 1 calc R . .
C23A C 0.4525(6) 1.1083(5) 0.4842(4) 0.0454(17) Uani 1 1 d . . .
C24A C 0.5450(6) 1.2770(5) 0.5136(5) 0.0479(17) Uani 1 1 d . . .
C25A C 0.6071(6) 1.3149(5) 0.6014(5) 0.0527(18) Uani 1 1 d . . .
H25A H 0.5997 1.2760 0.6320 0.063 Uiso 1 1 calc R . .
C26A C 0.6794(7) 1.4090(6) 0.6443(5) 0.060(2) Uani 1 1 d . . .
H26A H 0.7234 1.4347 0.7043 0.071 Uiso 1 1 calc R . .
C27A C 0.6888(8) 1.4675(6) 0.6003(6) 0.071(2) Uani 1 1 d . . .
H27A H 0.7389 1.5326 0.6302 0.085 Uiso 1 1 calc R . .
C28A C 0.6251(8) 1.4296(6) 0.5138(6) 0.070(2) Uani 1 1 d . . .
H28A H 0.6314 1.4689 0.4835 0.084 Uiso 1 1 calc R . .
C29A C 0.5516(7) 1.3350(6) 0.4699(5) 0.0569(19) Uani 1 1 d . . .
H29A H 0.5059 1.3097 0.4103 0.068 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1O 109.5 . . ?
C7 N1 N2 109.9(6) . . ?
C7 N1 C6 130.6(6) . . ?
N2 N1 C6 119.4(5) . . ?
C9 N2 N1 105.9(5) . . ?
C16 N3 N4 119.2(6) . . ?
N3 N4 C23 118.2(5) . . ?
N3 N4 H4N 120.9 . . ?
C23 N4 H4N 120.9 . . ?
C23 N5 C24 129.1(6) . . ?
C23 N5 H5N 115.5 . . ?
C24 N5 H5N 115.5 . . ?
C6 C1 C2 118.7(8) . . ?
C6 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C3 C2 C1 120.0(9) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.8(9) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.5(8) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 119.8(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.2(7) . . ?
C1 C6 N1 121.0(6) . . ?
C5 C6 N1 117.8(7) . . ?
O1 C7 C8 134.3(6) . . ?
O1 C7 N1 116.6(6) . . ?
C8 C7 N1 109.1(6) . . ?
C7 C8 C9 104.2(5) . . ?
C7 C8 C16 127.3(6) . . ?
C9 C8 C16 128.2(6) . . ?
N2 C9 C8 110.8(6) . . ?
N2 C9 C10 119.1(5) . . ?
C8 C9 C10 130.0(6) . . ?
C15 C10 C11 119.6(7) . . ?
C15 C10 C9 122.4(6) . . ?
C11 C10 C9 117.9(6) . . ?
C12 C11 C10 119.9(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.1(6) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.3(7) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C10 C15 C14 120.0(6) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N3 C16 C8 124.4(6) . . ?
N3 C16 C17 114.8(6) . . ?
C8 C16 C17 120.8(5) . . ?
C22 C17 C18 117.9(6) . . ?
C22 C17 C16 121.1(6) . . ?
C18 C17 C16 120.9(6) . . ?
C19 C18 C17 121.7(6) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.7(6) . . ?
C18 C19 Br1 121.0(5) . . ?
C20 C19 Br1 119.3(5) . . ?
C21 C20 C19 119.3(7) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.2(6) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.0(7) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
O2 C23 N5 124.7(6) . . ?
O2 C23 N4 119.8(6) . . ?
N5 C23 N4 115.5(6) . . ?
C25 C24 C29 120.3(6) . . ?
C25 C24 N5 123.4(6) . . ?
C29 C24 N5 116.3(6) . . ?
C24 C25 C26 118.3(7) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C27 C26 C25 121.5(7) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 121.0(7) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C27 C28 C29 119.3(7) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C28 C29 C24 119.5(7) . . ?
C28 C29 H29 120.2 . . ?
C24 C29 H29 120.2 . . ?
C7A O1A H1AO 109.5 . . ?
C7A N1A N2A 111.3(5) . . ?
C7A N1A C6A 129.5(6) . . ?
N2A N1A C6A 119.1(6) . . ?
C9A N2A N1A 104.5(5) . . ?
C16A N3A N4A 118.7(5) . . ?
C23A N4A N3A 115.2(5) . . ?
C23A N4A H4AN 122.4 . . ?
N3A N4A H4AN 122.4 . . ?
C23A N5AN C24A 129.2(5) . . ?
C23A N5AN H5A 115.4 . . ?
C24A N5AN H5A 115.4 . . ?
C6A C1A C2A 116.8(8) . . ?
C6A C1A H1A 121.6 . . ?
C2A C1A H1A 121.6 . . ?
C3A C2A C1A 121.6(8) . . ?
C3A C2A H2A 119.2 . . ?
C1A C2A H2A 119.2 . . ?
C2A C3A C4A 120.2(8) . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A H3A 119.9 . . ?
C5A C4A C3A 119.9(8) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C6A C5A C4A 118.7(7) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C5A C6A C1A 122.7(6) . . ?
C5A C6A N1A 117.0(6) . . ?
C1A C6A N1A 120.2(7) . . ?
O1A C7A N1A 119.5(6) . . ?
O1A C7A C8A 133.1(7) . . ?
N1A C7A C8A 107.4(6) . . ?
C7A C8A C9A 104.1(6) . . ?
C7A C8A C16A 127.9(7) . . ?
C9A C8A C16A 127.7(5) . . ?
N2A C9A C8A 112.6(5) . . ?
N2A C9A C10A 119.7(6) . . ?
C8A C9A C10A 127.7(5) . . ?
C11A C10A C15A 119.7(6) . . ?
C11A C10A C9A 119.8(5) . . ?
C15A C10A C9A 120.4(6) . . ?
C10A C11A C12A 120.0(6) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C13A C12A C11A 119.7(7) . . ?
C13A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?
C14A C13A C12A 120.7(6) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C13A C14A C15A 120.0(6) . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C10A C15A C14A 120.0(7) . . ?
C10A C15A H15A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
N3A C16A C8A 127.7(5) . . ?
N3A C16A C17A 111.9(6) . . ?
C8A C16A C17A 120.4(6) . . ?
C22A C17A C18A 119.6(5) . . ?
C22A C17A C16A 120.9(6) . . ?
C18A C17A C16A 119.4(5) . . ?
C19A C18A C17A 120.3(6) . . ?
C19A C18A H18A 119.9 . . ?
C17A C18A H18A 119.9 . . ?
C20A C19A C18A 120.8(6) . . ?
C20A C19A Br1A 120.1(5) . . ?
C18A C19A Br1A 119.0(5) . . ?
C19A C20A C21A 118.5(6) . . ?
C19A C20A H20A 120.8 . . ?
C21A C20A H20A 120.8 . . ?
C22A C21A C20A 120.9(6) . . ?
C22A C21A H21A 119.6 . . ?
C20A C21A H21A 119.6 . . ?
C17A C22A C21A 119.8(6) . . ?
C17A C22A H22A 120.1 . . ?
C21A C22A H22A 120.1 . . ?
O2A C23A N5AN 125.0(6) . . ?
O2A C23A N4A 118.4(6) . . ?
N5AN C23A N4A 116.6(5) . . ?
C25A C24A C29A 120.1(7) . . ?
C25A C24A N5AN 124.5(6) . . ?
C29A C24A N5AN 115.4(6) . . ?
C26A C25A C24A 119.8(7) . . ?
C26A C25A H25A 120.1 . . ?
C24A C25A H25A 120.1 . . ?
C25A C26A C27A 120.5(7) . . ?
C25A C26A H26A 119.7 . . ?
C27A C26A H26A 119.7 . . ?
C28A C27A C26A 119.2(8) . . ?
C28A C27A H27A 120.4 . . ?
C26A C27A H27A 120.4 . . ?
C27A C28A C29A 120.8(7) . . ?
C27A C28A H28A 119.6 . . ?
C29A C28A H28A 119.6 . . ?
C28A C29A C24A 119.5(7) . . ?
C28A C29A H29A 120.3 . . ?
C24A C29A H29A 120.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C19 1.895(6) . ?
O1 C7 1.354(8) . ?
O1 H1O 0.8400 . ?
O2 C23 1.243(8) . ?
N1 C7 1.373(7) . ?
N1 N2 1.377(8) . ?
N1 C6 1.420(9) . ?
N2 C9 1.341(8) . ?
N3 C16 1.303(7) . ?
N3 N4 1.366(7) . ?
N4 C23 1.371(7) . ?
N4 H4N 0.8800 . ?
N5 C23 1.342(8) . ?
N5 C24 1.414(7) . ?
N5 H5N 0.8800 . ?
C1 C6 1.377(10) . ?
C1 C2 1.397(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(9) . ?
C5 H5 0.9500 . ?
C7 C8 1.363(9) . ?
C8 C9 1.438(8) . ?
C8 C16 1.479(8) . ?
C9 C10 1.471(9) . ?
C10 C15 1.376(9) . ?
C10 C11 1.400(8) . ?
C11 C12 1.391(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(10) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.486(10) . ?
C17 C22 1.382(8) . ?
C17 C18 1.395(9) . ?
C18 C19 1.349(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.403(9) . ?
C20 C21 1.373(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(10) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C24 C25 1.388(9) . ?
C24 C29 1.401(9) . ?
C25 C26 1.390(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.357(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.373(11) . ?
C27 H27 0.9500 . ?
C28 C29 1.395(9) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
Br1A C19A 1.871(6) . ?
O1A C7A 1.326(8) . ?
O1A H1AO 0.8400 . ?
O2A C23A 1.265(7) . ?
N1A C7A 1.354(9) . ?
N1A N2A 1.390(7) . ?
N1A C6A 1.440(8) . ?
N2A C9A 1.327(7) . ?
N3A C16A 1.297(8) . ?
N3A N4A 1.388(6) . ?
N4A C23A 1.374(9) . ?
N4A H4AN 0.8800 . ?
N5AN C23A 1.336(8) . ?
N5AN C24A 1.406(9) . ?
N5AN H5A 0.8800 . ?
C1A C6A 1.377(9) . ?
C1A C2A 1.410(9) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.349(12) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.389(11) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(10) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.375(10) . ?
C5A H5A 0.9500 . ?
C7A C8A 1.398(8) . ?
C8A C9A 1.411(9) . ?
C8A C16A 1.475(9) . ?
C9A C10A 1.491(8) . ?
C10A C11A 1.382(9) . ?
C10A C15A 1.383(8) . ?
C11A C12A 1.394(9) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.372(10) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.370(10) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.387(9) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C16A C17A 1.519(8) . ?
C17A C22A 1.375(9) . ?
C17A C18A 1.391(8) . ?
C18A C19A 1.385(8) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.378(9) . ?
C20A C21A 1.399(9) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.393(8) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9500 . ?
C24A C25A 1.381(9) . ?
C24A C29A 1.391(9) . ?
C25A C26A 1.371(10) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.400(10) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.369(11) . ?
C27A H27A 0.9500 . ?
C28A C29A 1.382(11) . ?
C28A H28A 0.9500 . ?
C29A H29A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2A 0.84 1.75 2.562(6) 162.3 2_676
N4 H4N O2 0.88 2.42 3.066(7) 130.3 2_776
N4 H4N O1 0.88 2.66 3.164(7) 117.7 .
N5 H5N N3 0.88 2.16 2.593(7) 110.0 .
O1A H1AO O2 0.84 1.77 2.586(7) 165.0 2_676
N4A H4AN O2A 0.88 2.40 2.965(7) 122.8 2_676
N4A H4AN O1A 0.88 2.60 3.172(7) 123.6 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 1.7(7) . . . . ?
C6 N1 N2 C9 179.6(5) . . . . ?
C16 N3 N4 C23 -176.5(6) . . . . ?
C6 C1 C2 C3 0.8(12) . . . . ?
C1 C2 C3 C4 0.2(14) . . . . ?
C2 C3 C4 C5 0.6(13) . . . . ?
C3 C4 C5 C6 -2.4(11) . . . . ?
C2 C1 C6 C5 -2.6(11) . . . . ?
C2 C1 C6 N1 175.5(7) . . . . ?
C4 C5 C6 C1 3.5(11) . . . . ?
C4 C5 C6 N1 -174.7(6) . . . . ?
C7 N1 C6 C1 32.0(10) . . . . ?
N2 N1 C6 C1 -145.4(6) . . . . ?
C7 N1 C6 C5 -149.8(7) . . . . ?
N2 N1 C6 C5 32.8(9) . . . . ?
N2 N1 C7 O1 -178.4(5) . . . . ?
C6 N1 C7 O1 4.0(10) . . . . ?
N2 N1 C7 C8 0.2(7) . . . . ?
C6 N1 C7 C8 -177.3(6) . . . . ?
O1 C7 C8 C9 176.4(7) . . . . ?
N1 C7 C8 C9 -1.9(7) . . . . ?
O1 C7 C8 C16 2.0(12) . . . . ?
N1 C7 C8 C16 -176.3(6) . . . . ?
N1 N2 C9 C8 -2.9(7) . . . . ?
N1 N2 C9 C10 179.2(5) . . . . ?
C7 C8 C9 N2 3.1(7) . . . . ?
C16 C8 C9 N2 177.4(6) . . . . ?
C7 C8 C9 C10 -179.4(6) . . . . ?
C16 C8 C9 C10 -5.0(10) . . . . ?
N2 C9 C10 C15 150.2(6) . . . . ?
C8 C9 C10 C15 -27.2(10) . . . . ?
N2 C9 C10 C11 -27.1(8) . . . . ?
C8 C9 C10 C11 155.5(6) . . . . ?
C15 C10 C11 C12 0.2(9) . . . . ?
C9 C10 C11 C12 177.6(6) . . . . ?
C10 C11 C12 C13 0.6(10) . . . . ?
C11 C12 C13 C14 -0.2(10) . . . . ?
C12 C13 C14 C15 -1.0(11) . . . . ?
C11 C10 C15 C14 -1.4(10) . . . . ?
C9 C10 C15 C14 -178.6(6) . . . . ?
C13 C14 C15 C10 1.8(10) . . . . ?
N4 N3 C16 C8 -5.0(10) . . . . ?
N4 N3 C16 C17 177.0(5) . . . . ?
C7 C8 C16 N3 -54.6(10) . . . . ?
C9 C8 C16 N3 132.3(7) . . . . ?
C7 C8 C16 C17 123.3(7) . . . . ?
C9 C8 C16 C17 -49.8(9) . . . . ?
N3 C16 C17 C22 160.7(6) . . . . ?
C8 C16 C17 C22 -17.4(9) . . . . ?
N3 C16 C17 C18 -19.2(9) . . . . ?
C8 C16 C17 C18 162.7(6) . . . . ?
C22 C17 C18 C19 -3.7(10) . . . . ?
C16 C17 C18 C19 176.2(6) . . . . ?
C17 C18 C19 C20 5.0(10) . . . . ?
C17 C18 C19 Br1 -177.9(5) . . . . ?
C18 C19 C20 C21 -3.2(10) . . . . ?
Br1 C19 C20 C21 179.6(5) . . . . ?
C19 C20 C21 C22 0.2(11) . . . . ?
C20 C21 C22 C17 1.1(11) . . . . ?
C18 C17 C22 C21 0.5(10) . . . . ?
C16 C17 C22 C21 -179.4(6) . . . . ?
C24 N5 C23 O2 6.0(11) . . . . ?
C24 N5 C23 N4 -174.3(6) . . . . ?
N3 N4 C23 O2 179.4(6) . . . . ?
N3 N4 C23 N5 -0.4(8) . . . . ?
C23 N5 C24 C25 -12.2(11) . . . . ?
C23 N5 C24 C29 166.6(7) . . . . ?
C29 C24 C25 C26 1.8(11) . . . . ?
N5 C24 C25 C26 -179.5(6) . . . . ?
C24 C25 C26 C27 -0.7(11) . . . . ?
C25 C26 C27 C28 0.4(13) . . . . ?
C26 C27 C28 C29 -1.2(14) . . . . ?
C27 C28 C29 C24 2.3(13) . . . . ?
C25 C24 C29 C28 -2.6(12) . . . . ?
N5 C24 C29 C28 178.6(7) . . . . ?
C7A N1A N2A C9A -0.8(7) . . . . ?
C6A N1A N2A C9A 176.1(5) . . . . ?
C16A N3A N4A C23A 172.0(6) . . . . ?
C6A C1A C2A C3A -1.4(12) . . . . ?
C1A C2A C3A C4A 2.0(13) . . . . ?
C2A C3A C4A C5A -2.2(13) . . . . ?
C3A C4A C5A C6A 1.7(12) . . . . ?
C4A C5A C6A C1A -1.1(11) . . . . ?
C4A C5A C6A N1A 176.4(7) . . . . ?
C2A C1A C6A C5A 0.9(11) . . . . ?
C2A C1A C6A N1A -176.5(6) . . . . ?
C7A N1A C6A C5A 151.5(7) . . . . ?
N2A N1A C6A C5A -24.7(8) . . . . ?
C7A N1A C6A C1A -30.9(10) . . . . ?
N2A N1A C6A C1A 152.9(6) . . . . ?
N2A N1A C7A O1A 179.9(5) . . . . ?
C6A N1A C7A O1A 3.4(10) . . . . ?
N2A N1A C7A C8A 0.2(7) . . . . ?
C6A N1A C7A C8A -176.3(6) . . . . ?
O1A C7A C8A C9A -179.2(7) . . . . ?
N1A C7A C8A C9A 0.5(7) . . . . ?
O1A C7A C8A C16A -4.3(12) . . . . ?
N1A C7A C8A C16A 175.4(6) . . . . ?
N1A N2A C9A C8A 1.2(7) . . . . ?
N1A N2A C9A C10A 179.8(5) . . . . ?
C7A C8A C9A N2A -1.1(7) . . . . ?
C16A C8A C9A N2A -176.0(6) . . . . ?
C7A C8A C9A C10A -179.5(6) . . . . ?
C16A C8A C9A C10A 5.5(11) . . . . ?
N2A C9A C10A C11A 35.4(9) . . . . ?
C8A C9A C10A C11A -146.2(7) . . . . ?
N2A C9A C10A C15A -147.2(6) . . . . ?
C8A C9A C10A C15A 31.2(10) . . . . ?
C15A C10A C11A C12A 1.1(10) . . . . ?
C9A C10A C11A C12A 178.4(6) . . . . ?
C10A C11A C12A C13A -2.3(11) . . . . ?
C11A C12A C13A C14A 2.5(12) . . . . ?
C12A C13A C14A C15A -1.4(12) . . . . ?
C11A C10A C15A C14A 0.1(10) . . . . ?
C9A C10A C15A C14A -177.3(6) . . . . ?
C13A C14A C15A C10A 0.1(10) . . . . ?
N4A N3A C16A C8A 4.0(10) . . . . ?
N4A N3A C16A C17A -175.9(5) . . . . ?
C7A C8A C16A N3A 52.7(10) . . . . ?
C9A C8A C16A N3A -133.5(7) . . . . ?
C7A C8A C16A C17A -127.4(7) . . . . ?
C9A C8A C16A C17A 46.4(9) . . . . ?
N3A C16A C17A C22A -155.8(6) . . . . ?
C8A C16A C17A C22A 24.3(10) . . . . ?
N3A C16A C17A C18A 25.8(9) . . . . ?
C8A C16A C17A C18A -154.2(6) . . . . ?
C22A C17A C18A C19A 4.5(10) . . . . ?
C16A C17A C18A C19A -177.1(6) . . . . ?
C17A C18A C19A C20A -3.1(11) . . . . ?
C17A C18A C19A Br1A 176.0(5) . . . . ?
C18A C19A C20A C21A 0.0(12) . . . . ?
Br1A C19A C20A C21A -179.2(6) . . . . ?
C19A C20A C21A C22A 1.8(12) . . . . ?
C18A C17A C22A C21A -2.7(11) . . . . ?
C16A C17A C22A C21A 178.8(6) . . . . ?
C20A C21A C22A C17A -0.4(12) . . . . ?
C24A N5AN C23A O2A 0.3(11) . . . . ?
C24A N5AN C23A N4A 178.0(6) . . . . ?
N3A N4A C23A O2A -177.8(5) . . . . ?
N3A N4A C23A N5AN 4.3(8) . . . . ?
C23A N5AN C24A C25A -5.5(11) . . . . ?
C23A N5AN C24A C29A 175.7(6) . . . . ?
C29A C24A C25A C26A -2.5(11) . . . . ?
N5AN C24A C25A C26A 178.7(6) . . . . ?
C24A C25A C26A C27A 1.2(11) . . . . ?
C25A C26A C27A C28A -0.1(12) . . . . ?
C26A C27A C28A C29A 0.2(13) . . . . ?
C27A C28A C29A C24A -1.6(13) . . . . ?
C25A C24A C29A C28A 2.7(11) . . . . ?
N5AN C24A C29A C28A -178.4(7) . . . . ?
